Abstract

1-(1,3-benzodioxol-5-yl)-2-(methylamino)pentan-1-one falls under the category of a DEA Schedule I controlled substance. Substances classified under DEA Schedule I are characterized by having no currently accepted medical use in the United States, a lack of recognized safety for use under medical supervision, and a high potential for abuse. This compound is specifically recognized as a hallucinogenic substance.

This article aims to provide a comprehensive overview of Pentilon, delving into various aspects such as general information, physico-chemical properties, recreational pharmacology, observed effects and symptoms, commonly used street names, market prices, approximate dosage, potential dangerous interactions, legal status, the synthesis process of Pentilon, conclusions and a bibliography.

General Information About Pentilon [1-6]

Other synonyms names of Pentilon are: Pentylone; β-Keto-Methylbenzodioxolylpentanamine; βk-Methyl-K; βk-MBDP; methylenedioxypentedrone; 1‐(3,4‐methylenedioxyphenyl)‐2‐(methylamino)pentan‐1‐one; Methylbenzodioxolylpentanamine; 1-(benzo[d][1,3]dioxol-5-yl)-2-(MethylaMino)pentan-1-one

IUPAC Name of Pentilon: 1-(1,3-benzodioxol-5-yl)-2-(methylamino)pentan-1-one

CAS numbers are 698963-77-8 and 17763-01-8 (hydrochloride)

Physico-Chemical Properties of Pentilon [1-6]

• Molecular Formula C₁₃H₁₇NO₃
• Molar Weight 235.28 g/mol
• Boiling point 374.7±42.0 °C
• Melting Point 215-242 °C (hydrochloride)
• Color/Form: white to off-white crystalline powder
• Odor: Odourless

Structural formula present on Figure 1.

Figure 2 displays pills that potentially contain Pentilon.

General Information of Pentilon in Recreational Use and Pharmacology [7-10]

Pentylone, a stimulant originating from the 1960s, belongs to the substituted cathinone class, a subtype of substituted phenethylamines. This compound has been detected in certain powder samples traded under the name “NRG-1,” often mixed with various cathinone derivatives like flephedrone, MDPBP, MDPV and 4-MePPP. Additionally, it has been identified alongside 4-MePPP, marketed as “NRG-3”.

Users have reported side effects, including heightened paranoia, agitation, and difficulty sleeping, particularly evident at elevated doses with effects persisting for several days. Functionally, Pentylone serves as a serotonin-norepinephrine-dopamine reuptake inhibitor and a serotonin releasing agent. It has been observed that Pentylone exhibits hybrid activity, acting as a dopamine transporter (DAT) blocker while simultaneously functioning as a serotonin transporter substrate (SERT).

Effects and symptoms of Pentilon Use [7-10]

Synthetic cathinones exhibit effects akin to more prevalent stimulants like methamphetamine or MDMA (ecstasy), but they seem to possess higher potency, requiring smaller amounts to induce strong effects. Users note that synthetic cathinones generate less euphoria and psychedelic sensations compared to MDMA, and these effects dissipate more rapidly, prompting some individuals to consume larger quantities, escalating the risk of adverse effects and toxicity.

Elevated doses of synthetic cathinones may result in prolonged periods of insomnia, muscle twitching, heightened risk of agitation, paranoia, hallucinations, and toxic outcomes such as overheating and cardiovascular issues. Notably, many instances involve cathinones as apparent contaminants in products concurrently containing MDMA. In other cases, individuals have mistakenly purchased cathinones, assuming them to be substitutes for MDMA. Synthetic cathinones may manifest in various forms, including crystals, powders, tablets, or capsules.

Combining synthetic cathinones with other stimulants, such as MDMA in pills featuring the distinctive orange ‘Nike tick,’ amplifies the risk of toxic effects. Concurrent use of cathinones with psychedelics like LSD (acid) heightens the risk of dysphoria (bad trips), agitation, and behavioral disturbances, posing immediate dangers. Stimulants can also interact with various medications, including those prescribed for depression and anxiety. Common medications like ‘SSRIs,’ ‘SNRIs,’ and ‘TCAs’ may interact with stimulants, intensifying the risk of toxic effects. It is imperative to seek information about medications before combining them with other substances.

Individuals might ingest the initial pill, experience a minimal euphoric effect, mistakenly attributing it to a weak ecstasy tablet. Subsequently taking another pill could result in a substantial dose of pentylone, leading to effects lasting up to 36 hours. This could trigger agitation, insomnia, and paranoia, potentially necessitating medical intervention with persisting challenges such as elevated blood pressure and pulse.

All effects in different categories [7-10]

Generally speaking, in small doses the following effects may be experienced and may last for approximately 2-4 hours:

• rush of intense pleasure
• feeling happy, energetic and wanting to talk more
• intense connection with music
• restless sleep
• muscle tension (face and jaw)
• blurred vision
• light-headedness, dizziness
• distorted sense of time
• enlarged (dilated) pupils, blurred vision
• dry mouth, thirst
• sweating
• memory loss
• reduced appetite.

Higher doses may result in the following adverse affects:

• anxiety
• paranoia
• nose bleeds from snorting the drug
• stomach pains, nausea, vomiting
• skin rashes
• fast or irregular heartbeat
• high blood pressure and hot flushes
• strong urge to re-dose
• chest pain
• tremors, convulsions, death

Street Names, Prices and Approximate Dosage [7-10]

Prices: $510 for 100g, $2,100 for 1000g.

A subsequent post hoc Tukey’s test unveiled the following effectiveness rank order: NEP = NEPD > pentylone ≥ pentedrone cocaine 4-MeAP ≥4-MPD.

Pentylone’s impact on locomotor activity was observed at doses ranging from 5 to 30 mg/kg, with the 30 mg/kg dose representing a high quantity. 5 grams or 100 doses. Pentylone exhibited convulsions and lethality at a dose of 100 mg/kg.

Synthetic cathinones are commonly administered through snorting, swallowing, or injection. Orally ingested, the desired effects typically manifest within 15–45 minutes, while snorting reportedly leads to effects within a few minutes. The duration of effects is generally around 2-4 hours.

Dangerous interactions [10]

Combining synthetic cathinones with other substances can result in unpredictable effects, heightening the risk of harm. When paired with opioids, synthetic cathinones may elevate the risk of heart strain and respiratory arrest. Interactions between synthetic cathinones and MDMA can induce anxiety, heart strain, and intensified neurotoxic effects. Mixing synthetic cathinones with cocaine can trigger anxiety and heart strain, potentially escalating to stroke.

When synthetic cathinones are combined with benzodiazepines, there’s a potential for decreased or masked effects of both substances, raising the risk of overdose if one wears off before the other, contingent on the amount consumed. Additionally, combining synthetic cathinones with alcohol may result in individuals feeling less intoxicated due to the stimulant effects of amphetamines, potentially leading to increased alcohol consumption.

Legal Status [1]

Brazil: Category F2 (Banned Psychotropics)

Germany: Schedule I (Authorized for Scientific Use Only)

United Kingdom: Class B

United States: Schedule I

Considered illegal in Sweden and Finland

Synthesis of Pentylone [11]

Pentilon synthesis follows the eutilon synthesis method. The ketone species can be obtained through diverse pathways. Typically, cathinones are isolated in their salt forms, considering the inherent instability of the freebase. This method has also been utilized in crafting analogs of eutylone. The synthesis process initiates from a specified starting point and aligns with the scheme outlined in Figure 3.

Conclusion

Pentilon emerges as a stimulant with roots dating back to the 1960s, falling within the class of synthetic cathinones. Its association with Schedule I controlled substances indicates its potential for abuse and lack of recognized medical utility. The compound’s hybrid activity, acting as both a dopamine transporter blocker and a serotonin transporter substrate, adds a layer of complexity to its pharmacological profile. The risks associated with Pentilon use, including adverse effects and potential toxicity, underscore the importance of understanding its synthesis, properties, and legal implications for both public health and regulatory measures.

Bibliography

1. https://en.wikipedia.org/wiki/Pentylone
2. https://pubchem.ncbi.nlm.nih.gov/compound/60208608
3. https://www.chemspider.com/Chemical-Structure.29786041.html
4. https://www.lgcstandards.com/FR/en/p/CAY-9000746
5. https://www.lipomed-usa.com/en/pentylone-hcl
6. https://www.swgdrug.org/Monographs/Pentylone.pdf
7. Nuria Nadal-Gratacós, Ana Sofia Alberto-Silva etc. Structure–Activity Relationship of Novel Second-Generation Synthetic Cathinones: Mechanism of Action, Locomotion, Reward, and Immediate-Early Genes. Front. Pharmacol., Sec. Neuropharmacology, Vol. 12, 2021. https://doi.org/10.3389/fphar.2021.749429 https://www.frontiersin.org/articles/10.3389/fphar.2021.749429/full
8. https://www.health.vic.gov.au/drug-alerts/pentylone-in-orange-nike-tick-pills
9. https://www.chemistryworld.com/podcasts/pentylone/3009525.article
10. https://adf.org.au/drug-facts/synthetic-cathinones/
11. Critical Review Report: EUTYLONE. Expert Committee on Drug Dependence Forty-fourth Meeting Geneva, 11-15 October 2021. World Health Organization. Unedited-Advance copy 44th ECDD (2021): Eutylone. https://cdn.who.int/media/docs/default-source/essential-medicines/unedited-advance-copy-44th-ecdd-critical-review-report-eutylone.pdf?sfvrsn=ca370181_3&download=true